Temephos
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Basic Info
| Common Name | Temephos(F05893) |
| 2D Structure | |
| FRCD ID | F05893 |
| CAS Number | 3383-96-8 |
| PubChem CID | 5392 |
| Formula | C16H20O6P2S3 |
| IUPAC Name | [4-(4-dimethoxyphosphinothioyloxyphenyl)sulfanylphenoxy]-dimethoxy-sulfanylidene-$l^{5}-phosphane |
| InChI Key | WWJZWCUNLNYYAU-UHFFFAOYSA-N |
| InChI | InChI=1S/C16H20O6P2S3/c1-17-23(25,18-2)21-13-5-9-15(10-6-13)27-16-11-7-14(8-12-16)22-24(26,19-3)20-4/h5-12H,1-4H3 |
| Canonical SMILES | COP(=S)(OC)OC1=CC=C(C=C1)SC2=CC=C(C=C2)OP(=S)(OC)OC |
| Isomeric SMILES | COP(=S)(OC)OC1=CC=C(C=C1)SC2=CC=C(C=C2)OP(=S)(OC)OC |
| Synonyms |
Abathion
temephos
Temefos
3383-96-8
ABATE
Difos
Biothion
Difenphos
Bithion
Nimitex
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Organic thiophosphoric acids and derivatives |
| Subclass | Thiophosphoric acid esters |
| Intermediate Tree Nodes | Aryl thiophosphates |
| Direct Parent | Phenyl thiophosphates |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Phenyl thiophosphate - Diarylthioether - Phenoxy compound - Aryl thioether - Thiophosphate triester - Thiophenol ether - Benzenoid - Monocyclic benzene moiety - Sulfenyl compound - Thioether - Organic oxygen compound - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as phenyl thiophosphates. These are organothiophosphorus compounds that contain a thiophosphoric acid O-esterified with a phenyl group. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 466.458 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 10 |
| Complexity | 474 |
| Monoisotopic Mass | 465.99 |
| Exact Mass | 465.99 |
| XLogP | 6 |
| Formal Charge | 0 |
| Heavy Atom Count | 27 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.8882 |
| Human Intestinal Absorption | HIA+ | 0.9777 |
| Caco-2 Permeability | Caco2+ | 0.5199 |
| P-glycoprotein Substrate | Non-substrate | 0.7854 |
| P-glycoprotein Inhibitor | Inhibitor | 0.6201 |
| Non-inhibitor | 0.8997 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8606 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.6927 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7043 |
| CYP450 2D6 Substrate | Non-substrate | 0.7466 |
| CYP450 3A4 Substrate | Substrate | 0.5302 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.5452 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.5661 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9272 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.7357 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.9722 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7707 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.8714 |
| Non-inhibitor | 0.8339 | |
| AMES Toxicity | Non AMES toxic | 0.9041 |
| Carcinogens | Carcinogens | 0.5227 |
| Fish Toxicity | High FHMT | 0.9442 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8442 |
| Honey Bee Toxicity | High HBT | 0.9626 |
| Biodegradation | Not ready biodegradable | 0.9867 |
| Acute Oral Toxicity | III | 0.7751 |
| Carcinogenicity (Three-class) | Non-required | 0.6940 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -6.1777 | LogS |
| Caco-2 Permeability | 0.8637 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.7713 | LD50, mol/kg |
| Fish Toxicity | 0.8111 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.8437 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Cattle,Fat | Japan | 4ppm | |||
| Cattle,Muscle | Japan | 2ppm | |||
| Other Terrestrial Mammals,Muscle | Japan | 0.5ppm | |||
| Cattle,Edible Offal | Japan | 2ppm | |||
| Other Terrestrial Mammals,Kidney | Japan | 0.5ppm | |||
| Cattle,Kidney | Japan | 2ppm | |||
| Other Terrestrial Mammals,Liver | Japan | 0.5ppm | |||
| Cattle,Liver | Japan | 2ppm | |||
| Other Terrestrial Mammals,Fat | Japan | 3ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Larval Age and Nutrition Affect the Susceptibility of Culex quinquefasciatus(Diptera: Culicidae) to Temephos. | J Insect Sci | 2018 Mar 1 | 29718500 |
| Synergistic effect of entomopathogenic fungus Fusarium oxysporum extract in combination with temephos against three major mosquito vectors. | Pathog Glob Health | 2018 Feb | 29457957 |
| Larvicidal activity of Magnolia denudata seed hydrodistillate constituents and related compounds and liquid formulations towards two susceptible and two wild mosquito species. | Pest Manag Sci | 2016 May | 26085316 |
| Larvicidal activity and possible mode of action of four flavonoids and two fatty acids identified in Millettia pinnata seed toward three mosquito species. | Parasit Vectors | 2015 Apr 19 | 25928224 |
| Poly(ionic liquid) immobilized magnetic nanoparticles as new adsorbent forextraction and enrichment of organophosphorus pesticides from tea drinks. | J Chromatogr A | 2014 Sep 5 | 25022482 |
| Antimosquito properties of 2-substitutedphenyl/benzylamino-6-(4-chlorophenyl)-5-methoxycarbonyl-4-methyl-3,6-dihydropyrimidin--ium chlorides against Anopheles arabiensis. | Med Chem | 2014 Mar | 24506684 |
| Synthesis and crystal structure of new temephos analogues as cholinesteraseinhibitor: molecular docking, QSAR study, and hydrogen bonding analysis of solid state. | J Agric Food Chem | 2014 Jun 25 | 24893121 |
| Larvicidal activity of Cnidium monnieri fruit coumarins and structurally related compounds against insecticide-susceptible and insecticide-resistant Culex pipiens pallens and Aedes aegypti. | Pest Manag Sci | 2012 Jul | 22389164 |
| Larvicidal activity of Asarum heterotropoides root constituents against insecticide-susceptible and -resistant Culex pipiens pallens and Aedes aegypti and Ochlerotatus togoi. | J Agric Food Chem | 2010 Sep 22 | 20806890 |
| Solid-phase microextraction-liquid chromatography-mass spectrometry applied tothe analysis of insecticides in honey. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2008Jan | 17852391 |
| Isolation and characterization of bacteria capable of degrading polycyclicaromatic hydrocarbons (PAHs) and organophosphorus pesticides fromPAH-contaminated soil in Hilo, Hawaii. | J Agric Food Chem | 2007 Jul 11 | 17552538 |
| Esterases as biomarkers in Nereis (Hediste) diversicolor exposed to temephos and Bacillus thuringiensis var. israelensis used for mosquito control in coastalwetlands of Morbihan (Brittany, France). | Mar Environ Res | 2002 Sep-Dec | 12408646 |